12,13(E)-didehydro-13,14-dihydro-9-deoxy-PGD2 compounds

ABSTRACT

Prostaglandin analogs with the following cyclopentane ring structure: ##STR1## are disclosed along with intermediates useful in their preparation and processes for their preparation. These analogs are useful for some of the same pharmacological purposes as the prostaglandins, particularly and especially as blood platelet aggregation inhibitors.

The present application is a divisional application of Ser. No. 614,244,filed Sept. 17, 1975, now pending, U.S. Ser. No. 809,248, filed June 23,1977, and also a divisional application of Ser. No. 614,244, has nowissued as U.S. Pat. No. 4,099,014.

The present invention relates to prostaglandin analogs, for which theessential material constituting disclosure therefor is incorporated byreference here from U.S. Pat. No. 4,099,014.

I claim:
 1. A prostaglandin analog of the formula ##STR2## wherein m isone to 5, inclusive; wherein M₁ is ##STR3## wherein R₅ and R₆ arehydrogen or methyl, with the proviso that one of R₅ and R₆ is methylonly when the other is hydrogen;Wherein L₁ is ##STR4## wherein R₃ and R₄are hydrogen, methyl, or fluoro, being the same or different, with theproviso that one of R₃ and R₄ is fluoro only when the other is hydrogenor fluoro; Wherein R₁ is hydrogen, alkyl of one to 12 carbon atoms,inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7to 12 carbon atoms, inclusive, phenyl, phenyl substituted with one, two,or three chloro or alkyl of one to 3 carbon atoms, inclusive, or apharmacologically acceptable cation; and Wherein Z₆ is (1)cis--CH═CH--CH₂ --(CH₂)_(g) --CF₂ -- or (2) cis--CH═CH₂ --CH₂--(CH₂)_(g) --CH₂ --,wherein g is one, 2, or
 3. 2. A compound accordingto claim 1, wherein M₁ is ##STR5##
 3. A compound according to claim 1,wherein M₁ is ##STR6##
 4. A compound according to claim 3, where m is 3.5. A compound according to claim 4, wherein Z₆ is cis--CH═CH--CH₂--(CH₂)_(g) --CH₂ --.
 6. A compound according to claim 5, wherein g is3.
 7. A compound according to claim 5, wherein g is one.
 8. A compoundaccording to claim 7, wherein R₅ and R₆ are both hydrogen.
 9. A compoundaccording to claim 8, wherein R₃ and R₄ are both hydrogen. 10.13,14-Dihydro-12,13(E)-didehydro-9-deoxy-PGD₂, a compound according toclaim
 9. 11. A compound according to claim 8, wherein R₃ and R₄ are bothfluoro. 12.16,16-Difluoro-13,14-dihydro-12,13(E)-didehydro-9-deoxy-PGD₂, a compoundaccording to claim
 11. 13. A compound according to calim 4, wherein Z₆is cis--CH═CH--CH₂ ═(CH₂)_(g) --CF₂ --.
 14. A compound according toclaim 13, wherein g is
 3. 15. A compound according to claim 14, whereinR₅ and R₆ are both hydrogen.
 16. A compound according to claim 15,wherein R₃ and R₄ are both hydrogen. 17.2a,2b-Dihomo-2,2-difluoro-13,14-dihydro-12,13(E)-didehydro-9-deoxy-PGD₂,a compound according to claim
 15. 18. A compound according to claim 15,wherein R₃ and R₄ are both fluoro. 19.2a,2b-Dihomo-2,2,16,16-tetrafluoro-13,14-dihydro-12,13(E)-didehydro-9-deoxy-PGD₂,a compound according to claim
 17. 20. A compound according to claim 13,wherein g is one.
 21. A compound according to claim 20, wherein R₅ andR₆ are both hydrogen.
 22. A compound according to claim 21, wherein R₃and R₄ are both hydrogen. 23.2,2-Difluoro-13,14-dihydro-12,13(E)-didehydro-9-deoxy-PGD₂, a compoundaccording to claim
 22. 24. A compound according to claim 21, wherein R₃and R₄ are both fluoro. 25.2,2,16,16-Tetrafluoro-13,14-dihydro-12,13(E)-didehydro-9-deoxy-PGD₂, acompound according to claim 24.